Three Days in Boston

Must-See Spots in One of America's Oldest Cities

Boston in springtime is a bright and beautiful city in bloom. With the threat of a hefty snowstorm mostly over, a light jacket and good pair of walking shoes are all you need for a long weekend of exploring one of America’s oldest cities. 

No matter where you stay, getting to the heart of downtown Boston is easy with the MBTA Public Transit System. In fact, Boston is home to the first-ever subway system in the country. Tremont Street, which runs along the eastern edge of Boston Common, opened as a subway line in 1897 and is now recognized as a National Historic Landmark. 

If your time in Boston is short, but you want to get the most out of your visit, here are a few must-see spots you can tackle on foot. 

Downtown: Government Center and the Waterfront

Your first area of exploration should be the center of Boston’s historical significance: The Freedom Trail.  History buffs will enjoy an easy walk to see the Boston Massacre site, the Old State House, and Faneuil Hall, which opened in 1742 as a prominent meeting house and now functions as a historical site and vibrant marketplace alongside Quincy Market. Characterized by the statue of Samuel Adams out front, Faneuil Hall is perfectly situated a stone’s throw from Long Wharf and adjacent to The New England Holocaust Memorial, a stunning outdoor exhibit of six illuminated glass towers that stretch more than 50 feet high between Congress and Union Streets. Each of the towers is engraved with numbers representing the six million Jews who perished during Hitler’s Final Solution. 

Next to the Holocaust Memorial are some of the oldest restaurants in the city, including The Bell in Hand Tavern, which claims to be America’s oldest, marking its first pour of ale in 1795. The menu boasts lobster rolls, crab cakes, and fish and chips, along with other American favorites. 

While all the historical sites in Downtown Boston are easily discoverable on your own, particularly those places wedged between Government Center and the Waterfront, you might be interested in a guided tour via TheFreedomTrail.org. (The entirety of the trail stretches 2.5 miles and spotlights 16 major landmarks.) 

Boston Common and Beacon Hill

If the weather is particularly lovely, then Boston Common is a must for an afternoon picnic and stroll. Founded in 1634, Boston’s oldest public park consists of 50 acres of lush grass, flower beds, and trees alongside dozens of National Historic Landmarks, statues, plaques, and art installations. The central location of Boston Common makes it easy to see a few key spots along the way. 

On the northeast end of Boston Common is the Boston Athenaeum, a 19th-century library, museum, and cultural center, and behind it, the Granary Burying Ground, the resting place of Samuel Adams, Paul Revere, John Hancock, Robert Treat Paine, and Peter Faneuil, namesake of Faneuil Hall. Granary is the third oldest cemetery in Boston. (King’s Chapel Burying Ground, the city’s oldest, is two blocks north.) 

Book lovers will adore a peruse through the stacks in the Athenaeum, but they must also stop at the Brattle Bookshop, tucked away on West Street and home to three stories of used books and first editions. If the weather is dry, you can expect rows of used books on carts in the empty lot next door. No telling what gems you’ll discover. 

The northwest end of Boston Common is where you’ll find Cheers, the local bar and restaurant that needs no introduction but is a must-see for anyone who loved the hit television series. (Buy a commemorative pint glass for your pours at home.) After you get your fill of nostalgia, take a walk through historic Beacon Hill, a mostly residential neighborhood with some of the most beautiful colonial row houses and cobblestone streets you’ll ever see. Don’t leave the area before checking out Acorn Street, one of the most photographed streets in America. Its cobblestones are 200 years old. 

North End

No visit to Beantown is complete without going to the North End, or Boston’s Little Italy. As the city’s oldest residential neighborhood, it’s characterized by its architecture and some of the best Italian cuisine a foodie could want. From delis, pastry shops, and top-rated restaurants, the North End makes eating well in Boston an easy feat. (Regina Pizzeria is top-notch.)

History lovers will want to stop by the Old North Church, Paul Revere’s starting point for his Revolutionary ride, as well as Copp’s Hill Burying Ground, the city’s second oldest cemetery and resting place of Puritan minister Cotton Mather and Phillis Wheatley, the first African American author to publish a book of poetry. 

Boston is a welcoming, walkable city perfect for family vacations or a long weekend with your favorite person. 

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